Top 10 Holiday Songs That Will Hit You in the Feels

Videos by American Songwriter

Videos by American Songwriter

The holidays are often portrayed as an upbeat, festive time of year to celebrate another year over with family and friends. But it’s also a season of loneliness and nostalgia that can bring deep emotion to the surface. Thankfully we have the gift of music to help us process all the feelings. Here are 10 holiday songs bound to hit you in the feels this holiday season.

1. “River” – Joni Mitchell

“River” is a famously poignant song in Mitchell’s catalog. With just a piano and her haunting voice, Mitchell crafts a beautiful song around the idea of wanting to escape the life you’re in via a vast river to skate away on. The singer expresses vulnerability in the wake of a devastating breakup as she admits to being “hard to handle,” “selfish” and “sad,” juxtaposed with a festive Christmas backdrop as people sing songs of joy and peace. It’s a classic for a reason, serving as a fine demonstration of Mitchell’s delicate songwriting.

I’m so hard to handle
I’m selfish and I’m sad
Now I’ve gone and lost the best baby
That I ever had
Oh, I wish I had a river
I could skate away on
I wish I had a river so long
I would teach my feet to fly

2. “I’ll Be Home For Christmas” – Josh Groban

At first listen, “I’ll Be Home For Christmas” may not seem like a sad song, considering its popularity. But a close listen to the lyrics and it becomes clear that it’s sung from the perspective of a person who’s unsure if they’ll make it home to loved ones in time for the holiday. Groban offers a touching interpretation that reflects the penultimate line I’ll be home for Christmas/If only in my dreams as he incorporates the sound of servicemen and women sending heartfelt messages to loved ones they won’t get to be with on Christmas Day, making the listener ponder the hardship that is common for so many this time of year.

I am dreaming tonight
Of a place I love
Even more than I usually do
And although I know
It’s a long road back
I promise you

I’ll be home for Christmas

3. “Christmas Makes Me Cry” – Kacey Musgraves

The title says it all on this gem by country star Kacey Musgraves. What makes this song special is the way Musgraves sees those who are struggling and lonely during a time of year that’s about togetherness. She purely captures the feeling of loneliness, between missing the people we love and acknowledging the passage of time, noticing her parents getting a little older each year. The song directs the listener’s attention to those less fortunate—and is likely to bring a tear to your eye in the process.

It seems like everybody else is having fun
I wonder if I’m the only one
Who’s broken heart still has broken parts just wrapped in pretty paper
And it’s always sad seeing mom and dad getting a little grayer
And they always say, “Have a happy holiday”
And every year, I swear I sincerely try
Oh, but Christmas, it always makes me cry

4. “The Little Boy That Santa Claus Forgot” – Nat King Cole

Cole is known for being the voice of Christmas with his timeless tune, “The Christmas Song,” but he puts a damper on the cheerful season with “The Little Boy That Santa Claus Forgot.” The title gives away the ending, as the song tells the story of a fatherless young boy who didn’t get a visit from St. Nick. It’s possible you’ll feel as heartbroken as the child does, watching his friends play with their new toys before he wanders home to play with his “broken toys” from last year’s holiday. Despite the sad story, Cole’s voice still shines.

In the street, he envies all those lucky boys
Then wanders home to last year’s broken toys
I’m so sorry for that laddie
He hasn’t got a daddy
The little boy that Santa Claus forgot

5. “If We Make it Through December” – Merle Haggard

The country legend paints a picture of a harsh holiday season in “If We Make it Through December.” Haggard takes on the persona of a man who lost his job just before Christmas and is unsure if he’ll be able to provide his young daughter with the Christmas she deserves, which he drives home in the tear-inducing lines But my little girl don’t understand/Why daddy can’t afford no Christmas here. Adding insult to injury is the bitterly cold weather filled with snow, the singer envisioning a brighter future ahead—but only if they make it through the month.

Got laid off down at the factory
And their timing’s not the greatest in the world
Heaven knows I’ve been working hard
I wanted Christmas to be right for daddy’s girl

If we make it through December
Everything’s going to be alright, I know
It’s the coldest time of winter
And I shiver when I see the falling snow

6. “Same Old Lang Syne” – Dan Fogelberg

This old-fashioned Scottish song, traditionally titled “Auld Lang Syne,” can serve a multitude of purposes, such as somberly ringing in the new year or being played at other farewell events. Fogelberg injects some heart into the somber tune about reconnecting with a former girlfriend at the grocery store, leading them to a conversation catching up on life where the leading man learns that she married a man she doesn’t love and can’t tell if it’s “doubt or gratitude” he sees in her eyes. You really feel the pangs of lost love as the song ends with him watching her drive away, recalling fond memories of their love that no longer exists.

The beer was empty, and our tongues were tired
And running out of things to say
She gave a kiss to me as I got out
And I watched her drive away

Just for a moment, I was back at school
And felt that old familiar pain
And as I turned to make my way back home
The snow turned into rain

7. “Christmas Always Finds Me” – Ingrid Andress

Ingrid Andress is a true country songwriter in that she knows how to craft a lyric that will tug at the heartstrings. “Christmas Always Finds Me” does just that. Here, Andress captures the purity of the season’s spirit, noting that while she’s moved a lot and is no longer the young girl who dreamed of “rollerblades and pixie sticks,” no matter where life takes her, Christmas always finds me, she sings with quiet reverence. One can’t help but tear up at the song’s end as she sits alone, reminiscing on the warm memories of Christmases past that we all long for.

It takes me back to younger days
Of stockings on the fireplace
And presents stacked
And waiting by the tree
And even if I’m all alone
A million miles away from home
It shows up in warm memory

Another year older
Getting harder to believe
But somehow Christmas always find me

8. “Fairytale of New York” – The Pogues

The Pogues truly take us on a journey with their tragic tune, “Fairytale of New York.” The London-based band hones in on an Irish couple’s drunken conversation on Christmas Eve while in a jail cell designed specifically for people who are intoxicated. The banter devolves towards the end where they hurl insults at each other from “scumbag” and “maggot” to “old slut on junk,” realizing their dreams are crushed under the weight of drug and alcohol addiction. If you’re looking for holly jolly vibes, you definitely won’t find them here.

I could have been someone
Well so could anyone
You took my dreams from me
When I first found you
I kept them with me babe
I put them with my own
Can’t make it all alone
I’ve built my dreams around you

9. “House Without a Christmas Tree” – Craig Richey

North Carolina-based singer-songwriter Craig Richey turns the true story about going to his mother’s house, surprised to find that she had decided not to put up a tree following his father’s death, into a thoughtful acoustic song, which is captured in the lyrics I know you miss him/But this just don’t feel right to me/What’s a house without a Christmas tree. To make the season bright, he takes his mother tree shopping on Christmas Eve and they find the perfect one, turning the experience into a solid folk Christmas song that is a beautiful blend of reflection and sentimentality.

Mama’s face began to change
Softening she turned to me
What’s a house without a Christmas tree
She said daddy might have left us, I still feel a world of grief
But we’ve got each other and baby doll you reminded me
What’s a house without a Christmas tree

10. “What Are You Doing New Year’s Eve?” – Ella Fitzgerald

There’s a sense of longing that makes “What Are You Doing New Year’s Eve?” distinctly sad, as demonstrated by a woman who so desperately wants to ring in the new year with the person who’s caught her eye—and heart. We never know if her wish is fulfilled, adding to the song’s mysterious and somber nature.

Maybe I’m crazy to suppose
I’d ever be the one you chose
Out of the thousand invitations you received

Ah, but in case I stand one little chance
Here comes the jackpot question in advance
What are you doing New Year’s, New Year’s Eve?

Photo by Gilles Petard/Redferns

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